Wiley shot to art world fame over the last ten years painting street models, primarily young men of color whose sense of style catches his eye, into large-scale scenes reminiscent of classical heroic portraits. Think Jacque-Louis David’s “Napoleon Crossing the Alps,” but with a camoflage-clad, bandana’d young African American man on horseback instead (in his “Rumors of War” series, 2005-08).

“Two hundred or three hundred years ago, these portrait paintings served a very important purpose. They told the world something about the subject, which is they had status and they had power and they had money. So they were a form of propaganda, almost,” says Dupre, who grew up in Louisville and now lives in New York. “Kehinde, as a child, was very interested in painting and would go to the museums in Los Angeles, and he was just perplexed that there was a total lack of representation of African Americans in these paintings. It was a moment for him in launching his career in figuring out what he wanted to do with his work.”

For Wiley’s 2012 exhibit “An Economy of Grace,” the artist, who earned his MFA in art at Yale, decided to leave his comfort zone and paint a similar portrait series of women for the first time. Dupre was hooked – he knew from documenting Abramovic’s retrospective at MOMA that following a single project from spark to opening gives an art documentary a strong structure.

“He’s choosing to challenge himself, he’s choosing to do something new, and that was an interesting angle for the film,” says Dupre. “I think that it was daunting for him. Painting men and painting women, it’s actually a very different thing.”

Dupre’s new film “Kehinde Wiley: An Economy of Grace,” which won Best Short Documentary at South by Southwest earlier this year, covers the entire process of the series, starting with Wiley and his team approaching women of color — many of whom were understandably skeptical at first — in shopping centers in Brooklyn, Harlem and Queens. They were looking for a certain sense of style and confidence, not necessarily professional models.

The women who made it into the series of paintings came from different backgrounds — some knew of Wiley’s work, others didn’t — and they made compelling characters for the filmmakers, too.

“I had been there at the moment when we first laid eyes on each of these women on the streets of New York. Each of them had a special energy which I think spoke to Kehinde and he wanted to try to capture in the paintings,” says Dupre. “To go on this journey with each of them and to be there when they were able to see themselves through his eyes, that was great.”

Dupre’s film documents the artist’s process, from street-scouting the models to working with Givenchy designer Riccardo Tisci to design their gowns, to photographing them in poses reminiscent of classical portraits and painting the large-scale works in Wiley’s Beijing studio. The reveal, at Kelly’s New York gallery, is a particularly emotional scene, as the women see themselves in the scale and grandeur historically reserved for women of extreme privilege for the first time.

“I don’t think they quite knew what they were signing up for until they saw the paintings, because they’re so large — they’re enormous — so they’re quite amazing to behold,” says Dupre.

The documentary screens Wednesday, 7 p.m., at 21c Museum on West Main Street. It’s the only Louisville screening planned so far, as the film makes the festival rounds this summer in preparation for a PBS debut in the fall.